For the Dough:
3/4 cup unsalted butter, room temperature
2/3 cup sugar
2 1/2 teaspoons vanilla extract
2 1/4 cups all-purpose flour, sifted
Dash of salt
1-3 teaspoons water)
For the Filling:
1 cup Nutella store-bought or homemade
For the dough: Using a kitchen mixer, such as a KitchenAid fitted with a paddle attachment, add the butter and sugar and beat on high till light and fluffy, about 2-3 minutes. Add the egg and vanilla extract and mix to incorporate.
With the mixer on low, add the flour and salt and mix till a crumbly dough forms. If the dough is very dry and not coming together enough, add water, one teaspoon at a time till it comes together.
The dough should ideally be slightly tacky to the touch but not too sticky. If you added too much water, the dough is rather forgiving, just add a bit more flour until the right texture is achieved.
Remove the dough from the mixer and divide into two equal parts. For the dough into two flat disks, wrap in plastic wrap and allow to chill for about 2 hours.
Preheat the oven to 350 degrees F. Line two baking sheets with parchment paper and set aside. Remove the dough from the refrigerator and allow to warm up slightly before rolling.
Assembling the Hamantaschen: Once the dough has softened slightly, lightly flour your work surface and you’re rolling pin. Using a rolling pin roll the dough out into a large circle about ¼ inch thick. Note, the dough will be firm at first, that is as expected. If needed, pound out slightly with your rolling pin.
Using a 3-inch cookie cutter (or drinking glass) cut out circles in the dough, cutting as many as you can fit. Gather the scraps and repeat this process until all the dough has been used. Once all the dough has been cut out, depending on the exact thickness, you should have about 20-24 rounds.
Place a teaspoon of Nutella in the center of each dough circle. Assemble the Hamantashchen in three steps. First, grasp the left side of the circle and fold it towards the center to make a flap that covers the left third of the circle.
Next grasp the right side of the circle and fold it towards the center, overlapping the upper part of the left side flap to create a triangular tip at the top of the circle. A small triangle of filling should still be visible in the center.
Grasp the bottom part of the circle and fold it upward to create a third flap and complete the triangle. When you fold this flap up, be sure to tick the left side of this new flap overlap the right side of the triangle. Gently pinch each seam to firmly secure the shape and prevent the filling from coming out while baking. Use your fingers to carefully smooth out the uneven dough wherever needed.
Repeat the above process with the remaining dough circles. Place the filled Hamentaschen on the prepared baking sheets. Place in the oven and bake, rotating once, until the cookies are cooked through and only slightly showing coloration, about 10-12 minutes. Remove the Hamantaschen from the oven and allow to cool on a wire rack.
Hamantaschen should be stored in an airtight container to maintain freshness.